|
July 28, 2026 | View Online
|
 |
|
I told myself after our company work retreat that I'd slow down coming back to New York and keep it a chill weekend. But of course, I am constantly contradicting myself, and ended up busier than ever, bopping around Chinatown and Little Italy on a last-minute food tour and then taking a spontaneous day trip up to Tarrytown and Sleepy Hollow. I don’t actually know the definition of "relaxing," it seems.
I've shared my day trip below with some recs on where to eat, what to see, and how to get there without a car.
In today’s edition:
-
Are you daring enough to go on a mystery vacation?
-
JetBlue is overhauling fares from basic first to flexible economy
-
The Headless Horseman town is real – here’s my recs for a day trip from NYC
One day I’ll find my chill,
Kaylen
|
|
|
|
|
|
|
| TRAVEL
|
 |
|
Credit: Groupon
|
|
Groupon’s Mystery Getaway Offer Includes Hotel and Airfare
|
|
My finger has been hovering over the "buy" button on this Groupon page for ten minutes. Best case, I win a surprise trip to the coast of Italy. Worst case, I get a weekend in Indianapolis, which I'm sure is a fine city, just not the vibe I’m looking for if I’m leaving from LA. The city has to offer me more.
That's the pitch behind Groupon's Mystery Getaway deals: pay a flat fee, and Groupon books you a trip to a destination it won't reveal until after you've checked out. Europe, the US, the Caribbean, Asia, and more are all on the table. An algorithm draws your destination from a pool of 2,000 vouchers, matched to your dates, airport, and Gold, Silver, or Bronze tier. Once you pick your departure gate near your local airport, you'll pay exactly the price you see.
Everything you need to know about this mystery deal:
🎲 Your mystery destination gets drawn from the Gold, Silver, or Bronze tier, along with your trip length of 2, 4, or 7 nights. You can land anywhere from a major city abroad to a regional US getaway. Your travel dates and airport shape the draw.
✈️ Flights and hotel are covered. Every trip includes round-trip flights and a 3- or 4-star hotel.
👯 You can totally bring a friend along. The cost is per person, and you need at least 2 vouchers, since 2 travelers share a room. If you're going solo, you'll pay a $150 surcharge.
🚪 This season adds a new option: you can pick your gate. You choose Gate A, Gate B, or Gate C based on your nearest airport, and your price is based on your local flight market. Since my home airport is LAX, I’d pay $249 for a mystery trip.
📅 Travel dates: June 1 to December 20, 2026, and you must book by December 20. Blackout dates: July 1 to 6, August 29 to September 2, September 4 to 8, October 11 to 14, and November 21 to 30.
You can pick a date up to 90 days out, and you must book at least 14 days before you travel. Your preferred dates are used for the draw, but they aren't locked in as your departure date. Once your destination is revealed, the tour operator team works with you to confirm the exact departure date.
For more details on departure cities, costs, and how the tiers work, check out Groupon’s page with all the information. All this yapping, I’m just going to pull the trigger. I’d spend that $249 on a one-way ticket to the next state over anyway.
|
|
|
|
|
|
| TRAVEL SECRETS
|
 |
|
Fact: You Could Qualify for This Overseas Citizenship By Mail
|
|
Today, a new citizenship law has just granted millions of Americans dual citizenship!
Why care...?
If you’re eligible and secure this second citizenship, as an American, you could unlock—
This is now the fastest and easiest way to get a second passport for millions of U.S. citizens.
No trips overseas. No expensive lawyer fees. Apply from home.
Hurry: This is too good to last forever.
Don’t miss out.
Learn how to find out if you could qualify in 5 minutes...
|
|
|
|
|
|
| AIRLINES
|
 |
|
JetBlue's New First-Class Cabin, Plus a Fare Overhaul
|
|
I've mentioned before how JetBlue is one of my favorite domestic airlines for the little things that add up. Free Wi-Fi that works, seatback screens that don't feel like a relic from 2010, and legroom that doesn't punish you for flying coach. So when new updates come out from the airline, I’m all ears. Recent news is that JetBlue is changing its first-class cabin name to BlueFirst and bringing basic fares to more cabins.
💸 How the basic expansion to new cabins will work:
JetBlue's new BlueFirst cabin comes with a cheaper basic fare, which means no seat selection, change, and cancellation fees, and fewer points earned. EvenMore also gets a Base fare. Delta and United already did this to their premium cabins, so JetBlue is adopting the same game. More price points are good for buyers, but it also means "first class" doesn't guarantee much until you check the fare type. There is one exception, and that’s no Base fare in Mint, so business class stays untouched for now.
✈️ JetBlue’s new ticket types:
-
Base fare (cheapest): no seat selection, change/cancellation fees apply, travel credit only if you cancel, earns 1 point per $1. Available on Main, EvenMore, and BlueFirst, but not Mint.
-
Standard fare (the regular option): includes seat selection, no change/cancellation fees, travel credit if you cancel, earns 3 points per $1.
-
Flex fare (most expensive): includes seat selection, no change/cancellation fees, full refund to your original payment method, earns 3 points per $1.
A few other details to note: All fare types include a full-size carry-on bag. JetBlue's old "Blue Basic" fare is being renamed Main Basic. And lastly, passengers on Main Base or EvenMore Base don't get BlueHouse lounge access, even with JetBlue's premium credit card, which isn’t news, but good to know if you didn’t already.
|
|
|
|
|
|
| TRAVEL INSPO
|
 |
|
My Quick Day Trip to Tarrytown and Sleepy Hollow, NY
|
|
I've been in New York for nearly a month now, which I tend to do every summer. Life really does move in a New York minute; the pace of life doesn't slow down for anyone. So it's good to get out of the city once in a while to slow your breathing down. It’s why I took a quick train ride up to Tarrytown and Sleepy Hollow in Westchester County for a day trip this past weekend.
I took the Metro-North up from Grand Central to Tarrytown, which takes about 45 minutes on an express train, with only a handful of stops in between. Local trains take a bit longer (50 to 60 minutes) and make more stops along the way, but either way, it's one of the easiest escapes from the city, no car required because these towns are pretty walkable once you get off the train.
Tarrytown and Sleepy Hollow have shared the same ghost story for over 200 years. Washington Irving wrote "The Legend of Sleepy Hollow" in 1820, and the town liked the name enough to officially change itself from North Tarrytown to Sleepy Hollow in 1996. Tarrytown was a Hudson River trading post in the 1600s, later home to Gilded Age money like the Rockefellers, whose Kykuit estate still sits on the hill above town. Dutch settlers, a headless horseman, and one of America's wealthiest families, all within a 45-minute train ride of the city.
A small guide of my must-recs:
If you’re getting off at Tarrytown station, it’s a short walk up to Main Street where you’ll find a ton of good restaurants, delis, and vintage shops.
📍 A few vintage shops I loved: The Village Soccer Shop and Trilogy Consignment. At the latter, I snagged a really elegant resort dress made in Mexico for only $35.
🍴 Tarrytown eats:
-
Beekman Ale House for thin-crust pizza and a cold pint.
-
Bellas Restaurant is family-owned. has been around since 1980. You’d be a fool to not order the S’mores French toast and steak and eggs.
-
Basque - Authentic tapas bar with paellas and a Spanish wine list. Go for the classics like patatas bravas and garlic shrimp, but the paella (veggie, meat, and seafood options) is the reason people keep coming back.
-
Farmer and the Fish - Farm-to-table seafood dishes and refreshing cocktails. The restaurant has a beautiful deck with views right on the Hudson River, close to Sleepy Hollow's RiverWalk, with sightlines to the Tappan Zee Bridge and the Palisades across the water.
-
If you're willing to splurge, Blue Hill at Stone Barns is worth it. Set inside a working farm in Pocantico Hills, the restaurant skips a set menu and serves a multi-course tasting built around whatever's fresh that day. The tasting menu is $458 per person, plus tax and a 22% admin fee, and most reservations include a farm tour beforehand. For something more casual, the Blue Hill Cafeteria on-site serves a lunch tray for $48 per person, a much easier way to get a taste of the farm without the splurge.
🎃 Attractions to see in both towns:
-
Sleepy Hollow Cemetery & Old Dutch Church – Am I mentally okay for loving cemeteries? They’re so fascinating to me. Free to walk the grounds or take guided tours (like the Washington Irving-themed walk), which run around $20-25 per person.
-
Lyndhurst Mansion – $15 grounds pass (kids 6 and under free), tours inside start at $10.
-
Philipsburg Manor – Colonial-era manor and mill, part of Historic Hudson Valley's site network; check current ticket pricing on their site and book in advance.
-
Tarrytown Music Hall – Westchester's oldest theater, with a regular calendar of concerts and film screenings. Ticket prices vary by show.
Find my full list of recs and hotel stays on Google Maps here.
|
|
|
|
|
|
| METRO BY T-MOBILE
|
 |
|
Metro by T-Mobile is running a sweet deal now through September 30 — get the iPhone 16e on them with no activation fees!* Just bring your number and ID and sign up for the $50/month plan with AutoPay.
Shop now!
|
|
|
|
|
|
| TIKTOK OF THE DAY
|
 |
|
Dare I say the best tourism ad for China? And a JB soundtrack over it? Iconic.
|
|
|
|
|
|
|
|
|
|
|
Advertising Policy
Want to break our hearts? unsubscribe -
By receiving this email, you agree to our Terms & Privacy Policy, and consent to the collection and use of your information to improve our services.
© 2026 Dollar Flight Club, All Rights Reserved.
Dollar Flight Club, 600 1st Ave Ste 330 PMB 79116, Seattle, WA 98104-2246, United States
|
|
|
|
|